CA1177089A - Preparation d'alpha-tocopherol - Google Patents

Preparation d'alpha-tocopherol

Info

Publication number: CA1177089A
Authority: CA; Canada
Prior art keywords: acid; group; organic solvent; inert organic; amine
Prior art date: 1982-07-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000432451A

Other languages

English (en)

Inventor

Jeffrey L. Finnan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF Corp

Original Assignee

BASF Wyandotte Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-07-29

Filing date

1983-07-14

Publication date

1984-10-30

1983-07-14 Application filed by BASF Wyandotte Corp filed Critical BASF Wyandotte Corp

1984-10-30 Application granted granted Critical

1984-10-30 Publication of CA1177089A publication Critical patent/CA1177089A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 114
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 title claims abstract description 30
229940087168 alpha tocopherol Drugs 0.000 title claims abstract description 16
229960000984 tocofersolan Drugs 0.000 title claims abstract description 16
239000002076 α-tocopherol Substances 0.000 title claims abstract description 16
235000004835 α-tocopherol Nutrition 0.000 title claims abstract description 14
150000001412 amines Chemical class 0.000 claims abstract description 33
239000002253 acid Substances 0.000 claims abstract description 30
239000002841 Lewis acid Substances 0.000 claims abstract description 24
150000007517 lewis acids Chemical class 0.000 claims abstract description 24
125000001189 phytyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 claims abstract description 18
KEVYVLWNCKMXJX-ZCNNSNEGSA-N Isophytol Natural products CC(C)CCC[C@H](C)CCC[C@@H](C)CCC[C@@](C)(O)C=C KEVYVLWNCKMXJX-ZCNNSNEGSA-N 0.000 claims abstract description 17
AUFZRCJENRSRLY-UHFFFAOYSA-N 2,3,5-trimethylhydroquinone Chemical compound CC1=CC(O)=C(C)C(C)=C1O AUFZRCJENRSRLY-UHFFFAOYSA-N 0.000 claims abstract description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 61
239000003960 organic solvent Substances 0.000 claims description 41
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 36
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 33
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 24
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
239000007789 gas Substances 0.000 claims description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 21
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 20
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
239000011592 zinc chloride Substances 0.000 claims description 18
235000005074 zinc chloride Nutrition 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 17
125000001931 aliphatic group Chemical group 0.000 claims description 16
150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 15
ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 claims description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 14
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
238000009835 boiling Methods 0.000 claims description 14
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 14
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 14
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 14
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 14
RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 14
239000011541 reaction mixture Substances 0.000 claims description 13
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 11
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 claims description 10
229910000342 sodium bisulfate Inorganic materials 0.000 claims description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
239000000376 reactant Substances 0.000 claims description 9
229940042585 tocopherol acetate Drugs 0.000 claims description 9
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 9
-1 1-docosa-. namine Chemical compound 0.000 claims description 7
229910015900 BF3 Inorganic materials 0.000 claims description 7
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 7
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
229910017604 nitric acid Inorganic materials 0.000 claims description 7
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 7
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 claims description 7
239000008096 xylene Substances 0.000 claims description 7
ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 claims description 6
ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 claims description 6
NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 claims description 6
229950010007 dimantine Drugs 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
PTDWPHMHQZWGDT-UHFFFAOYSA-N n,n-dioctyldecan-1-amine Chemical compound CCCCCCCCCCN(CCCCCCCC)CCCCCCCC PTDWPHMHQZWGDT-UHFFFAOYSA-N 0.000 claims description 5
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 4
VPNOHCYAOXWMAR-UHFFFAOYSA-N docosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN VPNOHCYAOXWMAR-UHFFFAOYSA-N 0.000 claims description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims 12
KWZNMNHMFKPHBS-UHFFFAOYSA-N [B].FP(F)(F)=O Chemical compound [B].FP(F)(F)=O KWZNMNHMFKPHBS-UHFFFAOYSA-N 0.000 claims 6
RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 claims 4
BUHXFUSLEBPCEB-UHFFFAOYSA-N icosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN BUHXFUSLEBPCEB-UHFFFAOYSA-N 0.000 claims 4
241000237519 Bivalvia Species 0.000 claims 1
235000020639 clam Nutrition 0.000 claims 1
239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 abstract 1
BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 abstract 1
HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 abstract 1
BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 abstract 1
BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 abstract 1
GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 5
239000003377 acid catalyst Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229930003799 tocopherol Natural products 0.000 description 3
239000011732 tocopherol Substances 0.000 description 3
235000010384 tocopherol Nutrition 0.000 description 3
229960001295 tocopherol Drugs 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical group NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
GVJHHUAWPYXKBD-QLVXXPONSA-N (S,R,R)-alpha-tocopherol Chemical compound [H][C@@](C)(CCCC(C)C)CCC[C@@]([H])(C)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C GVJHHUAWPYXKBD-QLVXXPONSA-N 0.000 description 1
HJMZWDOOERQMND-ILWBRPEASA-N (e,7r,11r)-1-methoxy-3,7,11,15-tetramethylhexadec-2-ene Chemical compound COC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C HJMZWDOOERQMND-ILWBRPEASA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
101100463797 Rattus norvegicus Pgrmc1 gene Proteins 0.000 description 1
JIGCTXHIECXYRJ-ILWBRPEASA-N [(e,7r,11r)-3,7,11,15-tetramethylhexadec-2-enyl] acetate Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\COC(C)=O JIGCTXHIECXYRJ-ILWBRPEASA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
CNCBAEHAEKNSPZ-UHFFFAOYSA-N n-methylpentadecan-1-amine Chemical compound CCCCCCCCCCCCCCCNC CNCBAEHAEKNSPZ-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
VHGBWHGICRTHIQ-UHFFFAOYSA-N phytadiene Natural products CCCCCCCCCCCCCCCC=C(/C)C=C VHGBWHGICRTHIQ-UHFFFAOYSA-N 0.000 description 1
125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
JIGCTXHIECXYRJ-UHFFFAOYSA-N trans-phytol acetate Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)=CCOC(C)=O JIGCTXHIECXYRJ-UHFFFAOYSA-N 0.000 description 1
150000003772 α-tocopherols Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyrane Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA000432451A 1982-07-29 1983-07-14 Preparation d'alpha-tocopherol Expired CA1177089A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/403,085 US4639533A (en)	1982-07-29	1982-07-29	Alpha tocopherol process
US403,085		1982-07-29

Publications (1)

Publication Number	Publication Date
CA1177089A true CA1177089A (fr)	1984-10-30

Family

ID=23594421

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000432451A Expired CA1177089A (fr)	1982-07-29	1983-07-14	Preparation d'alpha-tocopherol

Country Status (3)

Country	Link
US (1)	US4639533A (fr)
JP (1)	JPS5962582A (fr)
CA (1)	CA1177089A (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2733977B1 (fr) *	1995-05-10	1997-07-04	Rhone Poulenc Nutrition Animal	Procede de preparation de phenols substitues
JP2002502360A (ja) *	1996-01-29	2002-01-22	ビーエーエスエフアクチェンゲゼルシャフト	ｄｌα―トコフェロールまたは酢酸ｄｌ―α―トコフェリルの製造方法
US6005122A (en) *	1996-12-23	1999-12-21	Basf Aktiengesellschaft	Preparation of α-tocopherol or α-tocopheryl acetate by reacting trimethylhydroquinone and phytol or isophytol, with recycling of the zinc halide condensation catalyst
KR100452291B1 (ko)	1999-12-14	2004-10-08	에스케이 주식회사	고수율 및 고순도로 ＤＬ-α-토코페롤를 제조하는 방법
KR100413373B1 (ko) *	2000-03-23	2003-12-31	에스케이 주식회사	ＤＬ-α-토코페롤 아세테이트의 제조방법
KR100408991B1 (ko) *	2000-03-23	2003-12-11	에스케이 주식회사	ＤＬ-α-토코페롤 아세테이트의 제조방법
WO2002034738A1 (fr)	2000-10-23	2002-05-02	Sk Corporation	Procede de preparation de dl-alpha-tocopherol avec un haut rendement

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2606830C3 (de) *	1976-02-20	1981-08-27	Basf Ag, 6700 Ludwigshafen	Verfahren zur Herstellung von Tocopherol
US4191692A (en) *	1976-02-20	1980-03-04	Basf Aktiengesellschaft	Manufacture of tocopherol
US4217285A (en) *	1976-09-29	1980-08-12	Nisshin Flour Milling Co., Ltd.	Process for the preparation of Dl-α-tocopherol of high purity
US4208334A (en) *	1978-12-22	1980-06-17	Hoffmann-La Roches Inc.	Process for preparation of α-tocopherol

1982
- 1982-07-29 US US06/403,085 patent/US4639533A/en not_active Expired - Lifetime
1983
- 1983-07-14 CA CA000432451A patent/CA1177089A/fr not_active Expired
- 1983-07-29 JP JP58137873A patent/JPS5962582A/ja active Granted

Also Published As

Publication number	Publication date
JPS5962582A (ja)	1984-04-10
JPH0435473B2 (fr)	1992-06-11
US4639533A (en)	1987-01-27

Legal Events

Date	Code	Title	Description
2001-10-31	MKEC	Expiry (correction)
2003-07-14	MKEX	Expiry

Publication	Publication Date	Title
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KR890002156A (ko)	1989-04-08	피롤로【3, 4-c】피롤의 개선된 제조방법
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JP4294875B2 (ja)	2009-07-15	トリエタノールアミンを精製する方法
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Gaertner	1967	Alkyl-2, 3-epoxypropylamines: Cyclodimerization and related eight-membered ring closures
CA1121370A (fr)	1982-04-06	Procede de fabrication d'esters tetraalkyliques d'acide orthosilicique
FI65420C (fi)	1984-05-10	Foerfarande foer framstaellning av 2,6-di-tert -butylfenol
GB1568559A (en)	1980-05-29	Manufacture of tocopherol
US4131614A (en)	1978-12-26	Process for preparing cis-hexahydrodibenzopyranones
EP0112297B1 (fr)	1986-10-29	Procédé pour la préparation d'acides bis(perfluoroalkyl-alkylthio)alcanoiques et lactones en dérivés
US4348523A (en)	1982-09-07	Preparation of thionamide compounds by sulfuration of imines
CA1242734A (fr)	1988-10-04	2,3-dihydrobenz-4-oxa-1-thiines
US4683307A (en)	1987-07-28	Process for the preparation of dodecamethylenebismelamine
US4451662A (en)	1984-05-29	Process for preparing 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran